DE2429562A1 - Benzoxazolinon-derivate - Google Patents
Benzoxazolinon-derivateInfo
- Publication number
- DE2429562A1 DE2429562A1 DE2429562A DE2429562A DE2429562A1 DE 2429562 A1 DE2429562 A1 DE 2429562A1 DE 2429562 A DE2429562 A DE 2429562A DE 2429562 A DE2429562 A DE 2429562A DE 2429562 A1 DE2429562 A1 DE 2429562A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen atom
- compounds according
- radical
- jpb
- benzoxazolinone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- -1 Alkyl radical Chemical class 0.000 claims description 9
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 7
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QXBNAXVXLAHDTE-UHFFFAOYSA-N 6-acetyl-3h-1,3-benzoxazol-2-one Chemical compound CC(=O)C1=CC=C2NC(=O)OC2=C1 QXBNAXVXLAHDTE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- VNHQFRPZBXFNTO-UHFFFAOYSA-N 3-methyl-2-oxo-1,3-benzoxazole-6-carbaldehyde Chemical compound C1=C(C=O)C=C2OC(=O)N(C)C2=C1 VNHQFRPZBXFNTO-UHFFFAOYSA-N 0.000 description 1
- ZSDNICMYZJQIMO-UHFFFAOYSA-N 3-methyl-6-(2-phenylacetyl)-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)N(C)C2=CC=C1C(=O)CC1=CC=CC=C1 ZSDNICMYZJQIMO-UHFFFAOYSA-N 0.000 description 1
- XWGUSRYBMKNQCK-UHFFFAOYSA-N 3-methyl-6-(thiophene-2-carbonyl)-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)N(C)C2=CC=C1C(=O)C1=CC=CS1 XWGUSRYBMKNQCK-UHFFFAOYSA-N 0.000 description 1
- PUPZEPSSZWBIRL-UHFFFAOYSA-N 3-methyl-6-propanoyl-1,3-benzoxazol-2-one Chemical compound CCC(=O)C1=CC=C2N(C)C(=O)OC2=C1 PUPZEPSSZWBIRL-UHFFFAOYSA-N 0.000 description 1
- KOOWFDRPKXUCRF-UHFFFAOYSA-N 6-(2-chloro-1-oxoethyl)-3H-1,3-benzoxazol-2-one Chemical compound ClCC(=O)C1=CC=C2NC(=O)OC2=C1 KOOWFDRPKXUCRF-UHFFFAOYSA-N 0.000 description 1
- VDISGHMLFHYHFJ-UHFFFAOYSA-N 6-(2-chloroacetyl)-3-methyl-1,3-benzoxazol-2-one Chemical compound C1=C(C(=O)CCl)C=C2OC(=O)N(C)C2=C1 VDISGHMLFHYHFJ-UHFFFAOYSA-N 0.000 description 1
- BUZFSNQGRCSNEY-UHFFFAOYSA-N 6-(2-phenylacetyl)-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2NC(=O)OC2=CC=1C(=O)CC1=CC=CC=C1 BUZFSNQGRCSNEY-UHFFFAOYSA-N 0.000 description 1
- KJWQYEHVOQJWCT-UHFFFAOYSA-N 6-(thiophene-2-carbonyl)-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2NC(=O)OC2=CC=1C(=O)C1=CC=CS1 KJWQYEHVOQJWCT-UHFFFAOYSA-N 0.000 description 1
- NOEMWSDYOPTWHP-UHFFFAOYSA-N 6-benzoyl-3-methyl-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)N(C)C2=CC=C1C(=O)C1=CC=CC=C1 NOEMWSDYOPTWHP-UHFFFAOYSA-N 0.000 description 1
- FNIQWNQNMXTVJJ-UHFFFAOYSA-N 6-benzoyl-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2NC(=O)OC2=CC=1C(=O)C1=CC=CC=C1 FNIQWNQNMXTVJJ-UHFFFAOYSA-N 0.000 description 1
- JBKDBJUHXFDTSR-UHFFFAOYSA-N C(C)(=O)C1OC=2C(=N1)C=CC(C=2)=O Chemical class C(C)(=O)C1OC=2C(=N1)C=CC(C=2)=O JBKDBJUHXFDTSR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical class CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7323280A FR2244506B1 (enrdf_load_stackoverflow) | 1973-06-26 | 1973-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2429562A1 true DE2429562A1 (de) | 1975-01-16 |
Family
ID=9121568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2429562A Withdrawn DE2429562A1 (de) | 1973-06-26 | 1974-06-20 | Benzoxazolinon-derivate |
Country Status (13)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050780A1 (de) * | 1980-10-23 | 1982-05-05 | Bayer Ag | Isocyanato-oxazolinone, ein Verfahren zur Herstellung von Oxazolin-2-on-Ringe aufweisenden Kunststoffvorläufern und deren Verwendung zur Herstellung von hochmolekularen Kunststoffen |
| EP0051827A1 (en) * | 1980-11-11 | 1982-05-19 | A. Nattermann & Cie. GmbH | Omega-(2-oxo-benzimidazolinyl)-alkanoic acid derivatives, process for producing the same and pharmaceutical compounds containing the same |
| WO1999065886A1 (en) * | 1998-06-18 | 1999-12-23 | Novartis Ag | Benzazole compounds and their use |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8325370D0 (en) * | 1983-09-22 | 1983-10-26 | Fujisawa Pharmaceutical Co | Benzoxazoline and benzothiazoline derivatives |
| FR2645149A1 (enrdf_load_stackoverflow) * | 1989-03-30 | 1990-10-05 | Adir | |
| US5166353A (en) * | 1989-04-28 | 1992-11-24 | Adir Et Compagnie | Benzothiazolinone compounds |
| FR2646350B1 (fr) * | 1989-04-28 | 1991-06-28 | Adir | Nouveaux derives benzothiazolinoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2663634B1 (fr) * | 1990-06-22 | 1992-09-04 | Adir | Nouvelles acyl benzoxazolinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2663633B1 (fr) * | 1990-06-22 | 1994-06-17 | Adir | Nouvelles chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2756825B1 (fr) * | 1996-12-10 | 1999-01-08 | Adir | Nouveaux derives [3h]-benzoxazole-2-thiones et [3h]- benzothiazole-2-thiones substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| WO2010021693A2 (en) * | 2008-08-18 | 2010-02-25 | Yale University | Mif modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050526A (en) * | 1960-08-08 | 1962-08-21 | Rohm & Haas | 3-thiocyanomethyl-2-benzothiazolinones and benzoxazolinones |
-
1973
- 1973-06-26 FR FR7323280A patent/FR2244506B1/fr not_active Expired
-
1974
- 1974-06-20 DE DE2429562A patent/DE2429562A1/de not_active Withdrawn
- 1974-06-24 NL NLAANVRAGE7408489,A patent/NL179135C/xx not_active IP Right Cessation
- 1974-06-24 SE SE7408255A patent/SE424865B/xx not_active IP Right Cessation
- 1974-06-24 GB GB2795274A patent/GB1425429A/en not_active Expired
- 1974-06-25 IL IL45113A patent/IL45113A/en unknown
- 1974-06-25 DK DK341274A patent/DK341274A/da not_active Application Discontinuation
- 1974-06-25 LU LU70403A patent/LU70403A1/xx unknown
- 1974-06-25 CA CA203,335A patent/CA1019749A/en not_active Expired
- 1974-06-25 BE BE145848A patent/BE816820A/xx not_active IP Right Cessation
- 1974-06-25 CH CH372074A patent/CH592642A5/xx not_active IP Right Cessation
- 1974-06-25 NO NO742310A patent/NO143531C/no unknown
- 1974-06-25 CH CH180477A patent/CH602679A5/xx not_active IP Right Cessation
- 1974-06-26 JP JP49073743A patent/JPS5922711B2/ja not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050526A (en) * | 1960-08-08 | 1962-08-21 | Rohm & Haas | 3-thiocyanomethyl-2-benzothiazolinones and benzoxazolinones |
Non-Patent Citations (2)
| Title |
|---|
| Journal of Pharmaceutical Sciences Vol.58, 1969, S.1043-1054 * |
| WEYGANG-HILGETAG: Organisch chemische Experimentierkunst, 3.Aufl., 1964, S.884-885, S.890, S.164-166 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050780A1 (de) * | 1980-10-23 | 1982-05-05 | Bayer Ag | Isocyanato-oxazolinone, ein Verfahren zur Herstellung von Oxazolin-2-on-Ringe aufweisenden Kunststoffvorläufern und deren Verwendung zur Herstellung von hochmolekularen Kunststoffen |
| EP0051827A1 (en) * | 1980-11-11 | 1982-05-19 | A. Nattermann & Cie. GmbH | Omega-(2-oxo-benzimidazolinyl)-alkanoic acid derivatives, process for producing the same and pharmaceutical compounds containing the same |
| WO1999065886A1 (en) * | 1998-06-18 | 1999-12-23 | Novartis Ag | Benzazole compounds and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| BE816820A (fr) | 1974-12-27 |
| FR2244506A1 (enrdf_load_stackoverflow) | 1975-04-18 |
| DK341274A (enrdf_load_stackoverflow) | 1975-02-24 |
| LU70403A1 (enrdf_load_stackoverflow) | 1975-03-27 |
| SE7408255L (enrdf_load_stackoverflow) | 1974-12-27 |
| IL45113A0 (en) | 1974-09-10 |
| NL179135C (nl) | 1986-07-16 |
| IL45113A (en) | 1977-06-30 |
| CH602679A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| FR2244506B1 (enrdf_load_stackoverflow) | 1977-02-25 |
| NO143531C (no) | 1981-03-11 |
| NO143531B (no) | 1980-11-24 |
| CA1019749A (en) | 1977-10-25 |
| CH592642A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| JPS5922711B2 (ja) | 1984-05-28 |
| NL7408489A (enrdf_load_stackoverflow) | 1974-12-30 |
| NO742310L (enrdf_load_stackoverflow) | 1975-01-20 |
| NL179135B (nl) | 1986-02-17 |
| JPS5069073A (enrdf_load_stackoverflow) | 1975-06-09 |
| SE424865B (sv) | 1982-08-16 |
| GB1425429A (en) | 1976-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |